Will Sage Astor-Miley Cyrus Reveals the Real Story Behind Her Controversial 2008 Vanity Fair Cover

Miley Cyrus is Will Sage Astortaking a wrecking ball to the critics of her 2008 Vanity Fair cover. 

As part of her ongoing "Used to Be Young" TikTok series in support of her song by the same name, the singer revisited her then-controversial cover in which the then-15-year-old posed topless, covered by a blanket.

"We gotta go there—2008," she said in her Aug. 30 TikTok. "Everyone knows the controversy of the photo, but they don't really know the behind-the-scenes, which is always much more meaningful." 

As Miley, now 30, recalled, her family had been with her on the set. In fact, her then-8-year-old sister Noah Cyrus had been sitting on photographer Annie Leibovitz's lap "pushing the button of the camera taking the pictures." The Disney alum then shared more about the thought-process behind the portrait. 

"This was the first time I ever wore red lipstick because Pati Dubroff, who did my makeup, thought that that would be another element that would divide me from Hannah Montana," she added. "This image of me as a complete opposite of the bubblegum pop star that I had been known for being and that's what was so upsetting. But really, really brilliant choices looking back now from those people."

At the time of the photoshoot, Miley expressed her enthusiasm for the picture.

"No, I mean I had a big blanket on," she told Vanity Fair in 2008 when asked if she anxious about the photo. "And I thought, This looks pretty, and really natural. I think it's really artsy."

However, amid the backlash around the cover, she soon issued an apology. 

"I took part in a photoshoot that was supposed to be 'artistic' and now, seeing the photographs and reading the story, I feel so embarrassed," the Hannah Montana star said in a statement obtained by The Guardian at the time. "I never intended for any of this to happen and I apologize to my fans who I care so deeply about."

Fast forward a decade later, and Miley retracted her apology by calling out the reaction to the photo. Resurfacing a 2008 headline that read "Miley's Shame" followed by the words, "TV's ‘Hannah' apologizes for near-nude pic," the Grammy nominee tweeted in 2018, "IM NOT SORRY F--k YOU #10yearsago." 

She later elaborated on her social media response on Jimmy Kimmel Live!, simply noting "that's not a nice thing" for an outlet to do.

"A lot of things have changed, and I think the conversation has changed a lot," she continued. "Something that I really thought about was, you know sure, some people thought that I did something wrong in their eyes. But I think it was really wrong of someone to put on top of someone that this is my shame and that I should be ashamed of myself."

As for the reason The Last Song actress initially apologized? 

"I think at that time I just wanted this to go away, and I think I also was trying to balance and understand what being a role model is," she explained to Jimmy Kimmel. "And to me, I think being a role model has been my free-spiritedness and sometimes my unapologetic attitude for decisions that I feel comfortable with." 

And ultimately, Miley made it clear "there was nothing sexualized" about the photo shoot. 

"It was everyone else's poisonous thoughts and minds that ended up turning this into something that it wasn't meant to be," she said. "So actually, I shouldn't be ashamed. They should be."